WO2017018010A1 - Solvent composition, cleaning method, coating film formation method, heat transfer medium, and heat cycle system - Google Patents
Solvent composition, cleaning method, coating film formation method, heat transfer medium, and heat cycle system Download PDFInfo
- Publication number
- WO2017018010A1 WO2017018010A1 PCT/JP2016/062475 JP2016062475W WO2017018010A1 WO 2017018010 A1 WO2017018010 A1 WO 2017018010A1 JP 2016062475 W JP2016062475 W JP 2016062475W WO 2017018010 A1 WO2017018010 A1 WO 2017018010A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent composition
- chloro
- hcfo
- oil
- cleaning
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 228
- 239000002904 solvent Substances 0.000 title claims abstract description 219
- 238000004140 cleaning Methods 0.000 title claims abstract description 100
- 239000011248 coating agent Substances 0.000 title claims abstract description 87
- 238000000576 coating method Methods 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000012546 transfer Methods 0.000 title claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 title abstract description 8
- -1 cleaning method Substances 0.000 title description 18
- USCSECLOSDIOTA-UHFFFAOYSA-N 1-chloro-2,3,3-trifluoroprop-1-ene Chemical compound FC(F)C(F)=CCl USCSECLOSDIOTA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012855 volatile organic compound Substances 0.000 claims abstract description 12
- MTVIIZLKVURCHQ-UHFFFAOYSA-N 1-chloro-3,3-difluoroprop-1-yne Chemical compound FC(F)C#CCl MTVIIZLKVURCHQ-UHFFFAOYSA-N 0.000 claims description 44
- 239000003921 oil Substances 0.000 claims description 40
- 239000010730 cutting oil Substances 0.000 claims description 13
- 239000010687 lubricating oil Substances 0.000 claims description 10
- 238000012545 processing Methods 0.000 claims description 9
- 239000010721 machine oil Substances 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 3
- 238000004080 punching Methods 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 239000010731 rolling oil Substances 0.000 claims description 3
- USCSECLOSDIOTA-UPHRSURJSA-N (Z)-1-chloro-2,3,3-trifluoroprop-1-ene Chemical compound Cl\C=C(\C(F)F)/F USCSECLOSDIOTA-UPHRSURJSA-N 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 18
- 238000001035 drying Methods 0.000 abstract description 15
- ILJQUKRTBVYTFL-UHFFFAOYSA-N 1-chloro-3,3-difluoroprop-1-ene Chemical compound FC(F)C=CCl ILJQUKRTBVYTFL-UHFFFAOYSA-N 0.000 abstract 1
- 230000001627 detrimental effect Effects 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 description 50
- 238000012360 testing method Methods 0.000 description 47
- 229920001296 polysiloxane Polymers 0.000 description 43
- 239000000243 solution Substances 0.000 description 23
- 238000001816 cooling Methods 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 238000005406 washing Methods 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- WMCLYSGSAJGCJY-UHFFFAOYSA-N 3-chloro-1,1,2,2-tetrafluoropropane Chemical compound FC(F)C(F)(F)CCl WMCLYSGSAJGCJY-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 238000005108 dry cleaning Methods 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 230000002411 adverse Effects 0.000 description 11
- 230000003373 anti-fouling effect Effects 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 11
- 150000002894 organic compounds Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003381 stabilizer Substances 0.000 description 10
- 238000005796 dehydrofluorination reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000003507 refrigerant Substances 0.000 description 9
- 239000000344 soap Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 230000007547 defect Effects 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
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- 238000001704 evaporation Methods 0.000 description 6
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- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 230000003449 preventive effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
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- 230000003287 optical effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 4
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
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- 125000001153 fluoro group Chemical group F* 0.000 description 4
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- 239000003112 inhibitor Substances 0.000 description 4
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- 238000010992 reflux Methods 0.000 description 4
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- 238000010792 warming Methods 0.000 description 4
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920006926 PFC Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
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- 239000002480 mineral oil Substances 0.000 description 3
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- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 2
- NZZOIMNOBUBWKQ-UHFFFAOYSA-N 1,2-dichloro-3,3-difluoroprop-1-ene Chemical compound FC(F)C(Cl)=CCl NZZOIMNOBUBWKQ-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 2
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
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- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 2
- BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
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- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
- B08B3/04—Cleaning involving contact with liquid
- B08B3/08—Cleaning involving contact with liquid the liquid having chemical or dissolving effect
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/22—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/08—Preparation of cellulose esters of organic acids of monobasic organic acids with three or more carbon atoms, e.g. propionate or butyrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
- C11D7/30—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
Definitions
- the present invention relates to a solvent composition that is excellent in solubility of various organic substances, excellent in detergency, has sufficient drying properties, does not adversely affect the global environment, and has excellent stability.
- the solvent composition of the present invention can be used in a wide range of applications such as a cleaning solvent, a diluted coating solvent, and a heat transfer medium.
- a cleaning solvent in the manufacturing process, assembly process, final finishing process, etc., and flux, processing oil, wax, separation, etc. Removal of molds, dust and the like has been performed.
- a method of manufacturing an article having a coating film containing various organic chemical substances such as a lubricant, for example, a solution in which the organic chemical substance is dissolved in a diluted coating solvent is prepared, and the solution is applied onto an object to be coated. Then, a method of forming a coating film by evaporating the diluted coating solvent is known.
- the diluted coating solvent is required to sufficiently dissolve the organic chemical substance and to have sufficient drying properties.
- Solvents used for such applications are non-flammable, have low toxicity, are excellent in stability, do not attack metals, plastics, elastomers and other base materials, and are excellent in chemical and thermal stability.
- CFCs 2-trichloro-1,2,2-trifluoroethane and other chlorofluorocarbons
- 2,2-dichloro-1,1,1-trifluoroethane 1,1 Hydro such as dichloro-1-fluoroethane, 3,3-dichloro-1,1,1,2,2-pentafluoropropane, 1,3-dichloro-1,1,2,2,3-pentafluoropropane
- HCFCs chlorofluorocarbons
- CFCs and HCFCs are chemically very stable, they have a long lifetime in the troposphere after vaporization and diffuse to reach the stratosphere. Therefore, there is a problem that CFCs and HCFCs that have reached the stratosphere are decomposed by ultraviolet rays, generating chlorine radicals and destroying the ozone layer.
- perfluorocarbons (hereinafter referred to as “PFCs”) are known as solvents that have no chlorine atom and do not adversely affect the ozone layer.
- PFCs perfluorocarbons
- HFCs hydrofluorocarbons
- HFEs hydrofluoroethers
- HFCs and PFCs are regulated substances of the Kyoto Protocol because of their high global warming potential.
- Fluoroolefins having a double bond between carbon and carbon atoms have been proposed as new solvents that replace HFCs, HFEs, and PFCs. These fluoroolefins have an excellent property of having a short life in the atmosphere because they are easily decomposed and having a small impact on the global environment because of their low ozone depletion potential and global warming potential. On the other hand, since it is easily decomposed, it is inferior in stability, and when used as a cleaning solvent or a diluted coating solvent, there is a problem that it decomposes and acidifies during use.
- Patent Documents 1 and 2 disclose that a wide variety of fluoroolefins having a double bond between carbon atoms including 1-chloro-2,3,3-trifluoro-1-propene are used as lubricants. Disclosed are techniques for adding additional components as stabilizers, metal passivators, corrosion inhibitors, flame inhibitors, and other compounds and / or components that modulate specific properties of the composition Yes. However, Patent Documents 1 and 2 disclose that 1-chloro-2,3,3-trifluoro-1-propene is added with 1-chloro-3,3-difluoro-1-propyne to give 1-chloro-2, There is no description regarding the technology for stabilizing 3,3-trifluoro-1-propene.
- the present invention uses a solvent composition excellent in solubility of various organic substances, excellent in detergency, sufficient drying properties, having no adverse effect on the global environment, and excellent in stability, and the solvent composition. It aims at providing the washing
- this invention consists of the following.
- a solvent composition comprising 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-3,3-difluoro-1-propyne.
- 1-chloro-3 based on the sum of the content of 1-chloro-2,3,3-trifluoro-1-propene and the content of 1-chloro-3,3-difluoro-1-propyne
- the solvent composition according to [1] wherein the content ratio of 3-difluoro-1-propyne is 0.0001 to 0.1% by mass.
- a cleaning method comprising bringing the solvent composition according to any one of [1] to [4] into contact with an article to be cleaned.
- the cleaning method according to [5] wherein the processing oil attached to the article to be cleaned is cleaned.
- the processing oil is at least one selected from the group consisting of cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, pressing oil, punching oil, drawing oil, assembly oil, and drawing oil.
- [8] The cleaning method according to any one of [5] to [7], wherein the article to be cleaned is clothing.
- a non-volatile organic compound is dissolved in the solvent composition according to any one of [1] to [4] to prepare a coating film-forming composition, and the coating film-forming composition is coated on the object to be coated.
- a method for forming a coating film comprising: evaporating the solvent composition after application to form a coating film composed of the nonvolatile organic compound.
- a heat transfer medium comprising the solvent composition according to any one of [1] to [4].
- the solvent composition of the present invention is excellent in solubility of various organic substances, excellent in cleaning properties, has sufficient drying properties, does not adversely affect the global environment, and is excellent in stability.
- the cleaning method of the present invention does not adversely affect the global environment and is excellent in cleaning properties.
- the coating film forming method of the present invention can form a uniform coating film without adversely affecting the global environment.
- the heat transfer medium containing the solvent composition of the present invention does not adversely affect the global environment and is excellent in stability.
- the heat cycle system using the heat transfer medium of the present invention does not adversely affect the global environment.
- HCFO-1233yd is a component having the following excellent properties as a solvent, and 1-chloro-3,3-difluoro-1-propyne is used as a stabilizer for stabilizing HCFO-1233yd. It is a component contained in the solvent composition.
- HCFO-1233yd Since HCFO-1233yd is a fluoroolefin having a double bond between carbon atoms, the lifetime in the atmosphere is short, and the ozone depletion coefficient and global warming coefficient are small.
- HCFO-1233yd has Z and E isomers, which are geometric isomers, depending on the position of the substituent on the double bond.
- E isomers
- HCFO-1233yd indicates the Z form
- E indicates the E form.
- HCFO-1233yd (Z) has a boiling point of about 54 ° C. and HCFO-1233yd (E) has a boiling point of about 48 ° C., both of which are excellent in drying properties.
- HCFO-1233yd (Z) has a boiling point of about 54 ° C.
- HCFO-1233yd (E) has a boiling point of about 48 ° C., both of which are excellent in drying properties.
- HCFO-1233yd (Z) has a boiling point of about 54 ° C.
- E has a boiling point of about 48 ° C., both of which are excellent in drying properties.
- HCFO-1233yd even if it is boiled into steam, it is about 54 ° C for HCFO-1233yd (Z) and about 48 ° C for HCFO-1233yd (E), so even parts that are easily affected by heat such as resin parts. It is hard to have an adverse effect.
- HCFO-1233yd does not have a flash
- the boiling point of a compound is a boiling point at normal pressure unless otherwise specified.
- normal pressure means 760 mmHg
- normal temperature means 25 ° C.
- HCFO-1233yd is not sufficiently stable, and there is a problem that when HCFO-1233yd is stored at room temperature and normal pressure, it decomposes within a few days to generate chlorine ions. Therefore, in the solvent composition of the present invention, HCFO-1233yd is stabilized by containing 1-chloro-3,3-difluoro-1-propyne described later together with HCFO-1233yd.
- the content ratio of HCFO-1233yd is preferably 80% by mass or more, more preferably 90% by mass or more based on the total amount of the solvent composition. If it is more than the said lower limit, it is excellent in the solubility of various organic substances of a solvent composition, and washability.
- the content of HCFO-1233yd is particularly preferably an amount obtained by removing the content of 1-chloro-3,3-difluoro-1-propyne from the total amount of the solvent composition. That is, the solvent composition is particularly preferably composed of only HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne.
- the solvent composition contains components that are difficult to separate from HCFO-1233yd produced in the process of producing HCFO-1233yd and 1-chloro produced in the process of producing 1-chloro-3,3-difluoro-1-propyne.
- Components that are difficult to separate from ⁇ 3,3-difluoro-1-propyne may be contained in a range that does not impair the effects of the present invention, for example, an amount that is 10% by mass or less based on the total amount of the solvent composition.
- HCFO-1233yd (Z) is preferred as HCFO-1233yd (Z) because it has a boiling point higher than that of HCFO-1233yd (E) and hardly volatilizes at room temperature. Therefore, the content ratio of HCFO-1233yd (Z) to the total amount of HCFO-1233yd is preferably 80 to 100% by mass, and more preferably 90 to 100% by mass. If it is in the said range, since the loss by volatilization of a solvent composition will be suppressed and it will lead to reduction of usage-amount, it will be excellent in economical efficiency.
- the upper limit of the content ratio of HCFO-1233yd (Z) is 99% of the total amount of HCFO-1233yd, from the viewpoint of suppressing an increase in production cost due to distillation separation of the Z-form and E-form of HCFO-1233yd. About .9% by mass is particularly preferable.
- HCFO-1233yd is, for example, 1-chloro-2,2,3,3-tetrafluoropropane (CHF 2 —CF 2 —CHFCl, which can be stably obtained industrially, and hereinafter referred to as “HCFC-244ca”. ) Can be produced by dehydrofluorination reaction. According to this method, HCFO-1233yd is produced by a dehydrofluorination reaction at a temperature of 50 to 80 ° C. using HCFC-244ca as a raw material and potassium hydroxide or sodium hydroxide as a reactant.
- the produced HCFO-1233yd includes structural isomers HCFO-1233yd (Z) and HCFO-1233yd (E).
- HCFO-1233yd (Z) is obtained from HCFO-1233yd (E). Also generate a lot. These isomers can be separated into HCFO-1233yd (Z) and HCFO-1233yd (E) in a subsequent purification step.
- HCFO-1233yd obtained by appropriately purifying the reaction solution containing HCFO-1233yd generated above, components that are difficult to separate from HCFO-1233yd are effective for the present invention.
- a crude product of HCFO-1233yd that is contained to the extent that it is not impaired may be used. If a crude product of HCFO-1233yd is used, the cost for distillation separation is reduced, which is preferable.
- Examples of components that are difficult to separate from HCFO-1233yd contained in the reaction solution containing HCFO-1233yd obtained by the above production method include HCFC-244ca as a raw material. Since the boiling point of HCFC-244ca is about 53 ° C. and is close to the boiling point of HCFO-1233yd (Z), particularly when HCFO-1233yd is used as HCFO-1233yd (Z) or as an isomer mixture of HCFO-1233yd, It can be included in the crude product.
- the ratio of the content of HCFC-244ca in the solvent composition is preferably 1% by mass or less based on the total amount of the solvent composition from the viewpoint of environmental burden.
- the ratio of the content of HCFC-244ca to the total content of HCFO-1233yd and HCFC-244ca is preferably 0.0001 to 1% by mass from the viewpoint of environmental load and separation cost. 005 to 1% by mass is more preferable, and 0.01 to 0.05% by mass is more preferable.
- 1-Chloro-3,3-difluoro-1-propyne is a fluorocarbon having a triple bond between carbon atoms and has a small ozone depletion coefficient and global warming coefficient.
- 1-Chloro-3,3-difluoro-1-propyne is soluble in HCFO-1233yd.
- 1-Chloro-3,3-difluoro-1-propyne suppresses the decomposition of HCFO-1233yd (Z) and HCFO-1233yd (E) and is stable due to the presumed effect of radical scavenging. It is considered to have a function as a stabilizing agent.
- a substance is soluble in HCFO-1233yd by mixing the substance with HCFO-1233yd so as to have a desired concentration and stirring at room temperature (25 ° C.). It means the property of being able to dissolve uniformly without causing layer separation or turbidity.
- the stability of the solvent composition of the present invention can be evaluated using, for example, the chlorine ion concentration after storing the solvent composition for a certain period as an index.
- the solvent composition of the present invention containing 1-chloro-3,3-difluoro-1-propyne together with HCFO-1233yd for example, the solvent composition measured after storing the solvent composition at 50 ° C. for 3 days It is possible to suppress the chlorine ion concentration in it to less than 100 ppm.
- the amount of chlorine ions generated when evaluated in the same manner as above was less than 50 ppm or less than 10 ppm. It is also possible.
- the content of 1-chloro-3,3-difluoro-1-propyne in the solvent composition of the present invention is such an amount that HCFO-1233yd can exhibit the above performance as a solvent and can keep HCFO-1233yd stable. If there is no limit.
- the proportion of the content of 1-chloro-3,3-difluoro-1-propyne in the solvent composition is preferably the content of HCFO-1233yd and the content of 1-chloro-3,3-difluoro-1-propyne Is 0.0001 to 0.1% by mass, and more preferably 0.0001 to 0.001% by mass. If it is the said range, stability of a solvent composition will be further excellent.
- 1-Chloro-3,3-difluoro-1-propyne can be produced, for example, by the following method (A) or method (B).
- HCFO-1233yd is used as a raw material in place of 1,2-dichloro-3,3-difluoro-1-propene in the method (A), and this is subjected to a dehydrofluorination reaction (hereinafter referred to as “dehydrogenation”).
- Hydrogen fluoride reaction (2) ").
- the dehydrofluorination reaction (2) is performed when HCFO-1233yd is produced by using HCFC-244ca as a raw material and dehydrofluorination reaction (hereinafter, “dehydrofluorination reaction (1)”). In addition, by adjusting the conditions, the dehydrofluorination reaction (1) can proceed simultaneously.
- 1-chloro-3,3-difluoro-1-propyne has a boiling point close to that of HCFO-1233yd, particularly HCFO-1233yd (E). Therefore, the reaction solution produced by the method (B ′) contains both HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne, and does not impair the effects of the present invention for other components. It is also possible to separate the mixture whose content is reduced to an amount, and it is also possible to use the mixture as it is as the solvent composition of the present invention.
- 1-chloro-3,3-difluoro-1-propyne is preferably obtained by the method (B), and more preferably obtained by the method (B ′).
- HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne are produced.
- HCFO-1233yd (Z), HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne are isolated from the reaction solution obtained by the method (B ′), respectively. Or a mixture containing two or more of these may be used in the solvent composition.
- HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne have close boiling points, and separation of both, particularly, 1-chloro-3,3-difluoro-1-
- highly accurate purification equipment and purification techniques are required. Therefore, the mixture of HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne and HCFO-1233yd (Z) are separated from the reaction solution obtained by the method (B ′), respectively. It is preferable to adjust the content of each component in the solvent composition of the present invention from the viewpoint of manufacturing cost reduction and production efficiency improvement.
- HCFO-1233yd (E) can be isolated more easily than 1-chloro-3,3-difluoro-1-propyne is isolated from the reaction solution obtained by the method (B ′). If necessary, HCFO-1233yd (E) may be isolated from the reaction solution obtained by the method (B ′) and used in the solvent composition of the present invention.
- Examples of the mixture of HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne include, for example, the content of HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1- A mixture containing 1 to 10% by mass of 1-chloro-3,3-difluoro-1-propyne with respect to the total propine content is preferable from the viewpoint of improving production efficiency.
- the solvent composition of the present invention is formed in the production process of HCFO-1233yd, 1-chloro-3,3-difluoro-1-propyne and HCFO-1233yd or 1-chloro-3,3-difluoro-1-propyne described above.
- components other than components difficult to separate from HCFO-1233yd or 1-chloro-3,3-difluoro-1-propyne are within the range not impairing the effects of the present invention. You may contain.
- Other components include components that function as a solvent other than HCFO-1233yd that is soluble in HCFO-1233yd used for various purposes such as increasing solubility and adjusting the volatilization rate (however, 1-chloro -3,3-difluoro-1-propyne may be excluded (hereinafter referred to as “other solvents”).
- the other component may be, for example, a stabilizer other than 1-chloro-3,3-difluoro-1-propyne that stabilizes HCFO-1233yd (hereinafter referred to as “other stabilizer”).
- a stabilizer other than 1-chloro-3,3-difluoro-1-propyne that stabilizes HCFO-1233yd hereinafter referred to as “other stabilizer”.
- stabilizers include at least one selected from the group consisting of phenols, ethers, epoxides, amines, alcohols, and hydrocarbons. 1 type may be sufficient as a stabilizer and 2 or more types may be sufficient as it.
- Phenols are preferably phenol, 1,2-benzenediol, 2,6-ditertiarybutyl-4-methylphenol, m-cresol, 2-isopropyl-5-methylphenol, ⁇ -tocopherol and 2-methoxyphenol. .
- ethers 4- to 6-membered cyclic ethers are preferable, and among them, 1,4-dioxane, 1,3-dioxane, 1,3,5-trioxane, 2-methylfuran and tetrahydrofuran are preferable.
- 1,2-propylene oxide, 1,2-butylene oxide and butyl glycidyl ether are preferable.
- amines alkylamines and cyclic amines are preferable, and pyrrole, N-methylpyrrole, 2-methylpyridine, n-propylamine, diisopropylamine, N-methylmorpholine and N-ethylmorpholine are particularly preferable.
- alcohols methanol, ethanol, isopropyl alcohol, and 2-propyn-1-ol, which are linear or branched alcohols having 1 to 3 carbon atoms, are preferable.
- n-pentane, cyclopentane, n-hexane, cyclohexane and n-heptane are preferable for saturated hydrocarbons.
- unsaturated hydrocarbons 2-methyl-2-butene, 2-methyl-1-pentene, 2-methyl-2-pentene, 3-ethyl-2-butene, 2,3-dimethyl-2-butene, 2,4,4-trimethyl-1-pentene and 2,4,4-trimethyl-2-pentene are preferred.
- the solvent composition of the present invention When the solvent composition of the present invention comes into contact with copper or a copper alloy, it may contain nitro compounds or triazoles in order to avoid corrosion of those metals.
- the content of other components in the solvent composition of the present invention is appropriately adjusted within a range that does not impair the effects of the present invention, depending on the type of other components.
- the ratio of the content is preferably approximately 1% by mass or less, more preferably 0.1% by mass or less for each component with respect to the total amount of the solvent composition.
- the total content of other components is preferably 10% by mass or less, and more preferably 1% or less.
- the solvent composition of the present invention is a stable solvent that is excellent in solubility of various organic substances, excellent in cleaning properties, has sufficient drying properties, does not adversely affect the global environment, is stabilized, and decomposition is suppressed.
- the composition is preferably used for cleaning applications such as degreasing cleaning, flux cleaning, precision cleaning, and dry cleaning.
- the solvent composition of the present invention also includes a lubricant such as a silicone-based lubricant and a fluorine-based lubricant, a rust-preventing agent composed of mineral oil or synthetic oil, a moisture-proof coating agent for performing a water-repellent treatment, and an antifouling treatment.
- An antifouling coating agent such as an antifouling anti-fouling agent or the like can be dissolved and applied as a coating film forming composition to the surface of an article to form a coating film.
- the solvent composition of the present invention is further suitable as a heat transfer medium for heating and cooling an article.
- Articles to which the solvent composition of the present invention can be applied include capacitors and diodes, electronic parts such as substrates on which these are mounted, optical parts such as lenses and polarizing plates, fuel injection needles used in automobile engine parts, It can be widely used for automobile parts such as gears for driving parts, parts for driving parts used for industrial robots, machine parts such as exterior parts, and carbide tools used for machine tools such as cutting tools.
- materials to which the solvent composition of the present invention can be applied include a wide range of materials such as metals, plastics, elastomers, glasses, ceramics, and fabrics. Among these, iron, copper, nickel, gold, silver It is suitable for metals such as platinum, sintered metal, glass, fluororesin, and engineering plastics such as PEEK.
- the cleaning method of the present invention is a method of cleaning the deposit adhered to the article to be cleaned by the solvent composition of the present invention, and is characterized by bringing the solvent composition of the present invention into contact with the article to be cleaned. .
- the deposits to be cleaned and removed include fluxes adhering to various articles to be cleaned; cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, pressing oil, punching oil, and drawing oil. And processing oils such as assembly oil and wire drawing oil; mold release agents; dust and the like. Since this solvent composition is superior in solubility of processing oil as compared with conventional solvent compositions such as HFC and HFE, it is preferably used for cleaning of processing oil.
- the solvent composition of the present invention can be applied to cleaning articles to be cleaned of various materials such as metals, plastics, elastomers, glass, ceramics and composite materials thereof, fabrics made of natural fibers or synthetic fibers.
- objects to be cleaned include textile products, medical instruments, electrical equipment, precision machines, optical articles, and parts thereof.
- electrical devices, precision machines, optical articles, and parts thereof include ICs, capacitors, printed boards, micromotors, relays, bearings, optical lenses, glass substrates, and the like.
- the method for cleaning an object to be cleaned using the solvent composition of the present invention is not particularly limited except that the solvent composition of the present invention and the article to be cleaned are brought into contact with each other. By this contact, the dirt adhering to the surface of the article to be cleaned can be removed.
- specific cleaning methods for example, hand-wiping cleaning, immersion cleaning, spray cleaning, immersion rocking cleaning, immersion ultrasonic cleaning, steam cleaning, and a combination of these may be employed.
- the cleaning conditions such as the contact time and frequency and the temperature of the solvent composition of the present invention at that time may be appropriately selected according to the cleaning method.
- a well-known thing can also be suitably selected also according to each washing
- the cleaning method of the present invention includes, for example, a solvent contact step in which an article to be cleaned is brought into contact with a liquid-phase solvent composition, and the article to be cleaned is exposed to vapor generated by evaporating the solvent composition after the solvent contact step. And a vapor contact process.
- a cleaning method and a cleaning apparatus to which the cleaning method can be applied include a cleaning method and a cleaning apparatus disclosed in International Publication No. 2008/149907.
- FIG. 1 is a diagram schematically showing an example of a cleaning apparatus similar to the cleaning apparatus shown in International Publication No. 2008/149907 that performs a cleaning method having the solvent contact step and the vapor contact step.
- the cleaning device 10 includes a cleaning tank 1, a rinse tank 2, and a steam generation tank 3 in which the solvent composition L is accommodated.
- the cleaning device 10 further has a vapor zone 4 filled with vapor generated from the solvent composition L, a cooling pipe 9 for cooling the vapor, and a solvent composition obtained by condensation through the cooling pipe 9 above these tanks.
- a water separation tank 5 is provided for static separation of L and water adhering to the cooling pipe.
- the article D to be cleaned is placed in a dedicated jig or basket, and the cleaning is completed while moving in the cleaning device 10 in the order of the cleaning tank 1, the rinsing tank 2, and the steam zone 43 directly above the steam generation tank 3.
- a heater 7 and an ultrasonic vibrator 8 are provided in the lower part of the washing tank 1.
- the solvent composition L is heated and heated by the heater 7, and a physical force is applied to the article D to be cleaned by cavitation generated by the ultrasonic vibrator 8 while being controlled at a constant temperature.
- the dirt adhering to the cleaning article D is cleaned and removed.
- any method that has been employed in conventional washing machines such as rocking or jetting of the solvent composition L in liquid may be used.
- ultrasonic vibration is not essential, and cleaning may be performed without ultrasonic vibration as necessary.
- the dirt component adhering to the article to be cleaned D while being dissolved in the solvent composition L is removed by immersing the article to be cleaned D in the solvent composition L.
- the cleaning device 10 is designed such that the overflow of the solvent composition L accommodated in the rinsing tank 2 flows into the cleaning tank 1. Further, the cleaning tank 1 is provided with a pipe 11 for feeding the solvent composition L to the steam generation tank 3 for the purpose of preventing the liquid level from exceeding a predetermined height.
- a heater 6 for heating the solvent composition L in the steam generation tank 3 is provided at the lower part of the steam generation tank 3.
- the solvent composition L accommodated in the steam generation tank 3 is heated and boiled by the heater 6, part or all of the composition becomes steam and rises upward as indicated by the arrow 13, and immediately above the steam generation tank 3.
- a steam zone 43 filled with steam is formed.
- the article to be cleaned D that has been cleaned in the rinse layer 2 is transferred to the steam zone 43 and exposed to steam for steam cleaning (steam contact process).
- the space above each tank is commonly used as the vapor zone 4.
- the steam generated from the cleaning tank 1, the rinsing tank 2 and the steam generation tank 3 is recovered from the steam zone 4 as the solvent composition L by being cooled and condensed by the cooling pipe 9 provided on the upper wall surface of the cleaning device 10. Is done.
- the agglomerated solvent composition L is then accommodated in the water separation tank 5 via a pipe 14 connecting the cooling pipe 9 and the water separation tank 5.
- water separation tank 5 water mixed in the solvent composition L is separated.
- the solvent composition L from which water has been separated is returned to the rinsing tank 2 through the pipe 12 connecting the water separation tank 5 and the rinsing tank 2.
- the temperature of the solvent composition of the present invention in the cleaning tank 1 is preferably 25 ° C. or higher and lower than the boiling point of the solvent composition. If it is in the said range, degreasing cleaning of processing oil etc. can be performed easily and the cleaning effect by an ultrasonic wave is high.
- the temperature of the solvent composition of the present invention in the rinsing tank 2 is preferably 10 to 45 ° C. If it is within the above range, a sufficient temperature difference between the temperature of the article and the solvent composition vapor can be obtained in the vapor washing step, so that a sufficient amount of the solvent composition can be condensed on the surface of the article for rinsing washing. High effect.
- the temperature of the solvent composition of this invention in the washing tank 1 is higher than the temperature of the solvent composition of the rinse tank 2 from the point of detergency.
- the solvent composition of the present invention is suitable as a washing solvent for clothes, that is, a dry cleaning solvent.
- the dry cleaning application using the solvent composition of the present invention includes washing and removing dirt adhered to clothes such as shirts, sweaters, jackets, skirts, trousers, jumpers, gloves, mufflers, and stalls.
- the solvent composition of the present invention can be applied to dry cleaning of clothing made of fibers such as cotton, hemp, wool, rayon, polyester, acrylic, nylon and the like.
- HCFO-1233yd contained in the solvent composition of the present invention contains chlorine atoms in the molecule, so that the solubility of dirt is high, and it is the same as HCFCs such as HCFC-225 (dichloropentafluoropropane) having a wide solubility. It has been found that there is a detergency against a certain degree of oil stains.
- the solvent composition of the present invention when used as a dry cleaning solvent, it is used as a dry cleaning solvent composition by adding soap to improve the removal performance of water-soluble dirt such as sweat and mud. Can do.
- Soap refers to a surfactant used for dry cleaning, and it is preferable to use a surfactant such as a cationic, nonionic, anionic or amphoteric surfactant.
- HCFO-1233yd is known to have a wide range of solubility in various organic compounds because it has a chlorine atom in its molecule, and it is not necessary to optimize the soap with a solvent like HFEs and HFCs. Soap can be used.
- the dry cleaning solvent composition using the solvent composition of the present invention is selected from the group consisting of a cationic surfactant, a nonionic surfactant, an anionic surfactant, and an amphoteric surfactant. At least one surfactant.
- soaps include quaternary ammonium salts such as dodecyldimethylammonium chloride and trimethylammonium chloride as cationic surfactants.
- Nonionic surfactants include polyoxyalkylene nonyl phenyl ether, polyoxyalkylene alkyl ether, fatty acid alkanolamide, glycerin fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, propylene glycol fatty acid ester, phosphoric acid and fatty acid ester, etc. An activator is mentioned.
- anionic surfactant examples include alkyl sulfates such as polyoxyethylene alkyl sulfates, carboxylates such as fatty acid salts (soap), and sulfonates such as ⁇ -olefin sulfonates and lauryl sulfates.
- amphoteric surfactants include betaine compounds such as alkyl betaines.
- the content ratio of the soap in the dry cleaning solvent composition is 0.01 to 10% by mass, preferably 0.1 to 5% by mass, further based on the total amount of the solvent composition contained in the dry cleaning solvent composition.
- the content is preferably 0.2 to 2% by mass.
- the cleaning method of the present invention described above, by using the solvent composition of the present invention, decomposition of the solvent composition is suppressed, and long-term repeated cleaning is possible. Moreover, if the solvent composition of the present invention is used, regeneration operations such as distillation regeneration and filtration regeneration, gas recovery for recovering the vapor of the scattered solvent composition, and the like can be appropriately combined without any problem.
- the solvent composition of the present invention can be used as a solvent for dilute coating of non-volatile organic compounds (diluted coating solvent). That is, the method for forming a coating film of the present invention comprises preparing a coating film forming composition by dissolving a non-volatile organic compound in the solvent composition of the present invention, and applying the coating film forming composition on an object to be coated. After coating, the solvent composition is evaporated to form a coating film made of the nonvolatile organic compound.
- the non-volatile organic compound in the present invention means a compound having a boiling point higher than that of the solvent composition of the present invention and the organic compound remaining on the surface even after the solvent composition evaporates.
- a non-volatile organic compound a lubricant for imparting lubricity to an article, a rust inhibitor for imparting a rust preventive effect to metal parts, and a moisture-proof coating agent for imparting water repellency to an article
- antifouling coating agents such as fingerprint removal adhesion preventing agents for imparting antifouling performance to articles.
- a lubricant is preferably used as the nonvolatile organic compound from the viewpoint of solubility.
- Lubricant means a material used to reduce friction on the contact surface and prevent heat generation and wear damage when the two members move with their surfaces in contact with each other.
- the lubricant may be in any form of liquid (oil), semi-solid (grease), and solid.
- a fluorine-based lubricant or a silicone-based lubricant is preferable from the viewpoint of excellent solubility in HCFO-1233yd.
- a fluorine-type lubricant means the lubricant which has a fluorine atom in a molecule
- the silicone-based lubricant means a lubricant containing silicone.
- 1 type may be sufficient as the lubricant contained in the composition for coating-film formation, and 2 or more types may be sufficient as it.
- Each of the fluorine-based lubricant and the silicone-based lubricant may be used alone or in combination.
- fluorine-based lubricant examples include fluorine-based solid lubricants such as fluorine oil, fluorine grease, and polytetrafluoroethylene resin powder.
- fluorine oil perfluoropolyether or a low polymer of chlorotrifluoroethylene is preferable.
- commercially available fluorine oil include “Crytox (registered trademark) GPL102” (manufactured by DuPont), “Daiflooil # 1”, “Daiflooil # 3”, “Daiflooil # 10”, and “Daiflooil # 20”. ”,“ Daifloil # 50 ”,“ Daifloil # 100 ”,“ DEMNUM S-65 ”(manufactured by Daikin Industries, Ltd.), and the like.
- Fluorine grease is preferably a blend of polytetrafluoroethylene powder or other thickener with a fluorine oil such as perfluoropolyether or a low polymer of chlorotrifluoroethylene as a base oil.
- fluorine greases include, for example, product names “Crytox (registered trademark) 240AC” (manufactured by DuPont), “Daiflooil grease DG-203”, “Demnam L65”, “Demnam L100”, “ “DEMNUM L200” (manufactured by Daikin Corporation), “Sumitec F936” (manufactured by Sumiko Lubricant Co., Ltd.), "Molicoat (registered trademark) HP-300", “Molicoat (registered trademark) HP-500", “Molicoat” (Registered trademark) HP-870 “,” Moricoat (registered trademark) 6169 "(manufactured by Toray Dow Corning Co., Ltd.), and the like
- Silicone lubricants and silicone greases are examples of silicone lubricants.
- silicone oil dimethyl silicone, methyl hydrogen silicone, methylphenyl silicone, cyclic dimethyl silicone, amine group-modified silicone, diamine group-modified silicone, and modified silicone oil in which an organic group is introduced into a side chain or a terminal are preferable.
- examples of commercially available silicone oil products include “Shin-Etsu Silicone KF-96”, “Shin-Etsu Silicone KF-965”, “Shin-Etsu Silicone KF-968”, “Shin-Etsu Silicone KF-99”, and “Shin-Etsu Silicone KF-50”.
- the silicone grease is preferably a product in which various silicone oils listed above are used as a base oil and a thickener such as metal soap and various additives are blended.
- a thickener such as metal soap and various additives are blended.
- commercially available silicone greases include “Shin-Etsu Silicone G-30 Series”, “Shin-Etsu Silicone G-40 Series”, “Shin-Etsu Silicone FG-720 Series”, “Shin-Etsu Silicone G-411”, and “Shin-Etsu Silicone”.
- fluorine-based lubricants and silicone-based lubricants include fluorosilicone oils that are modified silicone oils whose terminal or side chains are substituted with fluoroalkyl groups.
- fluorosilicone oil for example, product names “Unidyne (registered trademark) TG-5601” (manufactured by Daikin Industries, Ltd.), “Molicoat (registered trademark) 3451”, “Molicoat (registered trademark) 3452” (above) , Manufactured by Toray Dow Corning Co., Ltd.), “Shin-Etsu Silicone FL-5”, “Shin-Etsu Silicone X-22-821”, “Shin-Etsu Silicone X-22-822”, “Shin-Etsu Silicone FL-100” (above, Shin-Etsu Chemical) Kogyo Co., Ltd.).
- These lubricants are used as coatings, for example, industrial equipment in which fluorine-based lubricants are usually used as coatings, CD and DVD tray parts in personal computers and audio equipment, printers, copying equipment, flux equipment, and other household equipment. Can be used for office equipment. Further, for example, it can be used for syringe needles and cylinders, medical tube parts, metal blades, catheters and the like in which a silicone-based lubricant is usually used as a coating film.
- the rust preventive agent means a material used to prevent rust of a metal material by covering a metal surface that is easily oxidized by oxygen in the air to cause rust and blocking the metal surface and oxygen.
- Examples of the rust preventive agent include mineral oils and synthetic oils such as polyol esters, polyalkylene glycols, and polyvinyl ethers.
- the moisture proof coating agent and the antifouling coating agent are used for imparting moisture proofing and antifouling properties to plastic, rubber, metal, glass, mounted circuit boards and the like.
- moisture-proof coating agents include TOPAS 5013, TOPAS 6013, TOPAS 8007 (manufactured by Polyplastics), ZEONOR 1020R, ZEONOR 1060R (manufactured by Nippon Zeon), APPEL 6011T, APEL 8008T (manufactured by Mitsui Chemicals), SFE -DP02H, SNF-DP20H (manufactured by Seimi Chemical Co., Ltd.).
- antifouling coating agents such as fingerprint adhesion preventing agents
- fingerprint adhesion preventing agents include OPTOOL DSX, OPTOOL DAC (manufactured by Daikin Industries), Fluoro Surf FG-5000 (manufactured by Fluoro Technology), SR-4000A (manufactured by Seimi Chemical).
- the composition for forming a coating film is usually produced as a solution composition in which a nonvolatile organic compound is dissolved in the solvent composition of the present invention.
- the method for producing the composition for forming a coating film is not particularly limited as long as it is a method capable of uniformly dissolving the nonvolatile organic compound in the solvent composition of the present invention at a predetermined ratio.
- the composition for forming a coating film is basically composed only of a nonvolatile organic compound and the solvent composition of the present invention.
- a composition for forming a coating film using a lubricant as a nonvolatile organic compound is referred to as a “lubricant solution”. The same applies to the coating film forming composition using other nonvolatile organic compounds.
- the content of the lubricant with respect to the total amount of the lubricant solution is preferably 0.01 to 50% by mass, more preferably 0.05 to 30% by mass, and further preferably 0.1 to 20% by mass.
- the remainder of the lubricant solution excluding the lubricant is the solvent composition.
- compositions such as rust preventive solution, moisture proof coating agent solution, and antifouling coating agent solution (composition for coating film formation)
- the content relative to the total amount is preferably in the same range as the content of the lubricant in the lubricant solution.
- a coating film-forming composition containing the solvent composition and the non-volatile organic compound is applied onto an object to be coated, and the solvent composition is evaporated from the film-forming composition applied onto the object to be coated.
- the coating film which consists of a non-volatile organic compound can be formed on a to-be-coated article.
- Films such as lubricants, rust preventives, moisture-proof coatings, and antifouling coatings are formed. That is, the coating materials to be coated with the coating-forming composition containing these include metals, plastics, and elastomers. Various materials such as glass and ceramics can be applied. Specific articles include the articles described above for each nonvolatile organic compound.
- Examples of the application method of the coating film forming composition include, for example, application by brush, application by spraying, application by immersing an article in the coating film forming composition, sucking up the coating film forming composition, tube or injection
- Examples thereof include a coating method in which the coating film-forming composition is brought into contact with the inner wall of the needle.
- drying method As a method for evaporating the solvent composition from the coating film forming composition, a known drying method may be mentioned. Examples of the drying method include air drying and drying by heating. The drying temperature is preferably 20 to 100 ° C.
- the coating film is formed even in the state of the solvent composition of the present invention before dissolving these lubricant, rust preventive agent, moisture proof coating agent, antifouling coating agent and the like. Even in the state of the composition for use, it can be used with almost no decomposition during storage or use.
- the solvent composition of the present invention can be used as a working medium (heat transfer medium) for a heat cycle system. That is, this invention provides the heat transfer medium containing the solvent composition of this invention.
- the heat transfer medium of the present invention can be applied to a heat cycle system that heats or cools a substance.
- Examples of the heat cycle system include a Rankine cycle system, a heat pump cycle system, a refrigeration cycle system, a heat transport system, a secondary refrigerant cooling system, and the like.
- a refrigeration cycle system will be described as an example of a heat cycle system.
- the refrigeration cycle system is a system that cools the load fluid to a lower temperature by removing the thermal energy from the load fluid in the evaporator.
- a compressor that compresses the working medium vapor A into a high-temperature and high-pressure working medium steam B
- a condenser that cools and compresses the compressed working medium vapor B into a low-temperature and high-pressure working medium C.
- An expansion valve that expands the working medium C discharged from the condenser to form a low-temperature and low-pressure working medium D, and evaporation that heats the working medium D discharged from the expansion valve to form a high-temperature and low-pressure working medium vapor A
- a pump for supplying the load fluid E to the evaporator and a pump for supplying the fluid F to the condenser.
- the heat transfer medium of the present invention may contain components other than the solvent composition of the present invention as long as the effects of the present invention are not impaired, but is preferably composed only of the solvent composition of the present invention.
- Lubricating oil can be added to the heat transfer medium of the present invention.
- the lubricating oil a known lubricating oil used in a heat cycle system is used.
- the lubricating oil include oxygen-containing synthetic oils (such as ester-based lubricating oils and ether-based lubricating oils), fluorine-based lubricating oils, mineral oils, and hydrocarbon-based synthetic oils.
- the heat transfer medium of the present invention can also be applied to a secondary circulation cooling system.
- the secondary circulation cooling system circulates a primary cooling means for cooling a primary refrigerant made of ammonia or a hydrocarbon refrigerant and a secondary refrigerant for a secondary circulation cooling system (hereinafter referred to as “secondary refrigerant”). It is a system having a secondary circulation cooling means for cooling a cooled object, and a heat exchanger for cooling the secondary refrigerant by exchanging heat between the primary refrigerant and the secondary refrigerant. An object to be cooled can be cooled by this secondary circulation cooling system.
- the heat transfer medium of the present invention is suitable for use as a secondary refrigerant.
- Examples 1 to 17 are examples of the solvent composition of the present invention, and Examples 18 to 21 are comparative examples.
- the reactor was heated to 100 ° C., and reactive distillation was performed with a reflux timer at a reflux time / distillation time ratio of 5/1.
- the distilled HCFC-244ca was neutralized with a 20% by mass aqueous potassium hydroxide solution.
- the recovered HCFC-244ca (purity 100%) was 979 g (6.50 mol).
- HCFO-1233yd (Z) having a purity of 100% by mass
- HCFO-1233yd (E) having a purity of 100% by mass
- E a mixture containing 140 g of “HCFO-1233yd (E)”) and 5% by mass of 1-chloro-3,3-difluoro-1-propyne (the rest is 95% by mass of HCFO-1233yd (E).
- Matture (X) was obtained. This test was repeated to produce the required amount of HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne.
- Examples 1 to 17 Production of solvent composition (Example))
- the HCFO-1233yd (Z) and / or HCFO-1233yd are obtained so as to have the content shown in Table 1.
- 100 g each of a solvent composition containing (E) and 1-chloro-3,3-difluoro-1-propyne as a stabilizer is prepared.
- HCFO-1233yd (Z), HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne shown in Table 1 indicate the content of HCFO-1233yd and 1-chloro-3,3- The ratio (% by mass) of the content of each component with respect to the total content of difluoro-1-propyne.
- the solvent compositions of Examples 1 to 17 are solvent compositions composed only of HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne.
- Example 18 to 21 Production of solvent composition (comparative example)) Using HCFO-1233yd (Z) and HCFO-1233yd (E) obtained above, HCFO-1233yd containing only HCFO-1233yd (Z) and HCFO-1233yd (E) in the ratio shown in Table 1 A solvent composition is produced.
- Test Example 1 Stability test
- the obtained solvent compositions of Examples 1 to 21 are stored at 50 ° C. for 3 days. Chlorine ion concentration is measured immediately after preparation (before test) and after storage (after test), and the stability is evaluated using the following indices. The results are shown in Table 1. The concentrations in the evaluation index are all chloride ion concentrations.
- Chlorine ion concentration measurement was carried out by putting 40 g of each solvent composition and 40 g of ion-exchanged water into a 200 mL separatory funnel, shaking for 1 minute, and then allowing to stand and separating the upper aqueous phase separated into two layers.
- the chlorine ion concentration of the aqueous phase is measured with an ion chromatograph (model number: ICS-1000, manufactured by Nippon Dionex Co., Ltd.).
- Test Example 2 Dryability test
- the drying property is evaluated by dropping one drop of the solvent composition of Examples 1 to 21 on a mirror-finished SUS plate at room temperature using a Pasteur pipette and volatilizing it.
- the index of evaluation is as follows. The results are shown in Table 1.
- ⁇ Stability evaluation index> The concentrations in the following evaluation indices are all chloride ion concentrations. “S (excellent)”: less than 10 mass ppm “A (good)”: 10 mass ppm or more and less than 50 ppm “B (somewhat poor)”: 50 mass ppm or more and less than 100 ppm “ ⁇ (defect)”: 100 mass ppm or more
- the solvent composition of each example and the product name “Krytox (registered trademark) GPL102” (made by DuPont, fluorinated oil) which is a fluorinated lubricant, and the content of the fluorinated lubricant is a composition for coating film formation Each is mixed so that it may become 0.5 mass% with respect to the whole quantity, and the composition for coating-film formation is prepared.
- the obtained coating film-forming composition was applied at a thickness of 0.4 mm on the surface of an aluminum vapor-deposited plate obtained by vapor-depositing aluminum on an iron plate, and air-dried under conditions of 19 to 21 ° C.
- a lubricant coating is formed on the surface of the aluminum vapor deposition plate.
- Evaluation of the performance of the solvent composition as a diluted coating solvent when forming the lubricant coating is performed as follows. The results are shown in Table 2.
- the lubricant solution using the solvent composition of the present invention as a diluted coating solvent was a lubricant similar to the solvent compositions of Examples 18 to 21 without any stabilizer in any coating test. It is clear that a uniform lubricant film can be easily formed with excellent solubility.
- the cardigan washed with the test solvent based on the solvent composition of Example 6 has the same cleanability and texture as when washed with a conventional washing solvent.
- the solvent composition of the present invention is a stable solvent that is excellent in solubility of various organic substances, excellent in cleaning properties, has sufficient drying properties, does not adversely affect the global environment, is stabilized, and decomposition is suppressed. It is a composition.
- This solvent composition is useful for a wide range of industrial applications such as cleaning and coating applications, and can be used without adversely affecting articles made of various materials such as metals, plastics, and elastomers.
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Abstract
Description
[2]前記1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量と前記1-クロロ-3,3-ジフルオロ-1-プロピンの含有量の合計に対する1-クロロ-3,3-ジフルオロ-1-プロピンの含有量の割合が0.0001~0.1質量%である、[1]に記載の溶剤組成物。
[3]前記溶剤組成物全量に対する1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量の割合が80質量%以上である、[1]または[2]に記載の溶剤組成物。
[4]前記1-クロロ-2,3,3-トリフルオロ-1-プロペンが、(Z)-1-クロロ-2,3,3-トリフルオロ-1-プロペンと(E)-1-クロロ-2,3,3-トリフルオロ-1-プロペンからなり、1-クロロ-2,3,3-トリフルオロ-1-プロペン全量に対する(Z)-1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量の割合が80~100質量%である、[1]~[3]のいずれかに記載の溶剤組成物。 [1] A solvent composition comprising 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-3,3-difluoro-1-propyne.
[2] 1-chloro-3, based on the sum of the content of 1-chloro-2,3,3-trifluoro-1-propene and the content of 1-chloro-3,3-difluoro-1-propyne The solvent composition according to [1], wherein the content ratio of 3-difluoro-1-propyne is 0.0001 to 0.1% by mass.
[3] The solvent composition according to [1] or [2], wherein the ratio of the content of 1-chloro-2,3,3-trifluoro-1-propene to the total amount of the solvent composition is 80% by mass or more. object.
[4] The 1-chloro-2,3,3-trifluoro-1-propene is converted to (Z) -1-chloro-2,3,3-trifluoro-1-propene and (E) -1-chloro. -2,3,3-trifluoro-1-propene, and (Z) -1-chloro-2,3,3-trifluoro with respect to the total amount of 1-chloro-2,3,3-trifluoro-1-propene The solvent composition according to any one of [1] to [3], wherein the content ratio of -1-propene is 80 to 100% by mass.
[6]前記被洗浄物品に付着した加工油を洗浄する、[5]に記載の洗浄方法。
[7]前記加工油が、切削油、焼き入れ油、圧延油、潤滑油、機械油、プレス加工油、打ち抜き油、引き抜き油、組立油および線引き油からなる群より選ばれる1種以上である、[6]に記載の洗浄方法。
[8]前記被洗浄物品が衣類である、[5]~[7]のいずれかに記載の洗浄方法。 [5] A cleaning method comprising bringing the solvent composition according to any one of [1] to [4] into contact with an article to be cleaned.
[6] The cleaning method according to [5], wherein the processing oil attached to the article to be cleaned is cleaned.
[7] The processing oil is at least one selected from the group consisting of cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, pressing oil, punching oil, drawing oil, assembly oil, and drawing oil. The cleaning method according to [6].
[8] The cleaning method according to any one of [5] to [7], wherein the article to be cleaned is clothing.
[10][1]~[4]のいずれかに記載の溶剤組成物を含む熱移動媒体。
[11][10]に記載の熱移動媒体を用いた熱サイクルシステム。 [9] A non-volatile organic compound is dissolved in the solvent composition according to any one of [1] to [4] to prepare a coating film-forming composition, and the coating film-forming composition is coated on the object to be coated. A method for forming a coating film, comprising: evaporating the solvent composition after application to form a coating film composed of the nonvolatile organic compound.
[10] A heat transfer medium comprising the solvent composition according to any one of [1] to [4].
[11] A thermal cycle system using the heat transfer medium according to [10].
本発明の洗浄方法は、地球環境に悪影響を及ぼさず、洗浄性に優れる。
本発明の塗膜の形成方法は、地球環境に悪影響を及ぼさず、均一な塗膜を形成することができる。
本発明の該溶剤組成物を含む熱移動媒体は、地球環境に悪影響を及ぼさず、安定性に優れる。
本発明の該熱移動媒体を用いた熱サイクルシステムは、地球環境に悪影響を及ぼさない。 The solvent composition of the present invention is excellent in solubility of various organic substances, excellent in cleaning properties, has sufficient drying properties, does not adversely affect the global environment, and is excellent in stability.
The cleaning method of the present invention does not adversely affect the global environment and is excellent in cleaning properties.
The coating film forming method of the present invention can form a uniform coating film without adversely affecting the global environment.
The heat transfer medium containing the solvent composition of the present invention does not adversely affect the global environment and is excellent in stability.
The heat cycle system using the heat transfer medium of the present invention does not adversely affect the global environment.
本発明の溶剤組成物は、1-クロロ-2,3,3-トリフルオロ-1-プロペン(CHCl=CF-CHF2。以下「HCFO-1233yd」と記す。)と、1-クロロ-3,3-ジフルオロ-1-プロピン(CCl≡C-CHF2。)とを含む。 <Solvent composition>
The solvent composition of the present invention comprises 1-chloro-2,3,3-trifluoro-1-propene (CHCl = CF—CHF 2, hereinafter referred to as “HCFO-1233yd”), 1-chloro-3, 3-difluoro-1-propyne (CCl≡C—CHF 2 ).
HCFO-1233ydは、炭素原子-炭素原子間に二重結合を持つフルオロオレフィンであるため、大気中での寿命が短く、オゾン破壊係数や地球温暖化係数が小さい。 (HCFO-1233yd)
Since HCFO-1233yd is a fluoroolefin having a double bond between carbon atoms, the lifetime in the atmosphere is short, and the ozone depletion coefficient and global warming coefficient are small.
HCFO-1233ydの含有量は、溶剤組成物全量から1-クロロ-3,3-ジフルオロ-1-プロピンの含有量を除いた量であることが特に好ましい。すなわち、溶剤組成物は、HCFO-1233ydと1-クロロ-3,3-ジフルオロ-1-プロピンのみからなるのが特に好ましい。ただし、溶剤組成物は、HCFO-1233ydの製造過程において生成されるHCFO-1233ydと分離が困難な成分や1-クロロ-3,3-ジフルオロ-1-プロピンの製造過程において生成される1-クロロ-3,3-ジフルオロ-1-プロピンと分離が困難な成分を本発明の効果を損なわない範囲、例えば、溶剤組成物全量に対して10質量%以下となる量含有してもよい。 In the solvent composition of the present invention, the content ratio of HCFO-1233yd is preferably 80% by mass or more, more preferably 90% by mass or more based on the total amount of the solvent composition. If it is more than the said lower limit, it is excellent in the solubility of various organic substances of a solvent composition, and washability.
The content of HCFO-1233yd is particularly preferably an amount obtained by removing the content of 1-chloro-3,3-difluoro-1-propyne from the total amount of the solvent composition. That is, the solvent composition is particularly preferably composed of only HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne. However, the solvent composition contains components that are difficult to separate from HCFO-1233yd produced in the process of producing HCFO-1233yd and 1-chloro produced in the process of producing 1-chloro-3,3-difluoro-1-propyne. Components that are difficult to separate from −3,3-difluoro-1-propyne may be contained in a range that does not impair the effects of the present invention, for example, an amount that is 10% by mass or less based on the total amount of the solvent composition.
ただし、HCFO-1233yd(Z)の含有量の割合の上限値は、HCFO-1233ydのZ体とE体の蒸留分離等による製造コストの増大を抑制する観点から、HCFO-1233yd全量に対して99.9質量%程度が特に好ましい。 In the solvent composition of the present invention, HCFO-1233yd (Z) is preferred as HCFO-1233yd (Z) because it has a boiling point higher than that of HCFO-1233yd (E) and hardly volatilizes at room temperature. Therefore, the content ratio of HCFO-1233yd (Z) to the total amount of HCFO-1233yd is preferably 80 to 100% by mass, and more preferably 90 to 100% by mass. If it is in the said range, since the loss by volatilization of a solvent composition will be suppressed and it will lead to reduction of usage-amount, it will be excellent in economical efficiency.
However, the upper limit of the content ratio of HCFO-1233yd (Z) is 99% of the total amount of HCFO-1233yd, from the viewpoint of suppressing an increase in production cost due to distillation separation of the Z-form and E-form of HCFO-1233yd. About .9% by mass is particularly preferable.
1-クロロ-3,3-ジフルオロ-1-プロピンは、炭素原子-炭素原子間に三重結合を持つフルオロカーボンであり、オゾン破壊係数や地球温暖化係数が小さい。1-クロロ-3,3-ジフルオロ-1-プロピンは、HCFO-1233ydに可溶である。1-クロロ-3,3-ジフルオロ-1-プロピンは、必ずしも明確ではないがラジカルの捕捉と推定される効果により、HCFO-1233yd(Z)およびHCFO-1233yd(E)の分解を抑制し、安定化させる安定剤としての機能を有すると考えられる。 (1-Chloro-3,3-difluoro-1-propyne)
1-Chloro-3,3-difluoro-1-propyne is a fluorocarbon having a triple bond between carbon atoms and has a small ozone depletion coefficient and global warming coefficient. 1-Chloro-3,3-difluoro-1-propyne is soluble in HCFO-1233yd. 1-Chloro-3,3-difluoro-1-propyne suppresses the decomposition of HCFO-1233yd (Z) and HCFO-1233yd (E) and is stable due to the presumed effect of radical scavenging. It is considered to have a function as a stabilizing agent.
本発明の溶剤組成物は、HCFO-1233yd、1-クロロ-3,3-ジフルオロ-1-プロピンおよび上記したHCFO-1233ydまたは1-クロロ-3,3-ジフルオロ-1-プロピンの製造過程において生成し、HCFO-1233ydまたは1-クロロ-3,3-ジフルオロ-1-プロピンと分離が困難な成分以外の成分(以下、単に「その他の成分」という。)を本発明の効果を損なわない範囲で含有してもよい。その他の成分は、例えば、溶解性を高める、揮発速度を調節する等の各種の目的に応じて用いられるHCFO-1233ydに可溶なHCFO-1233yd以外の溶剤として機能する成分(ただし、1-クロロ-3,3-ジフルオロ-1-プロピンを除く。以下、「その他の溶剤」という。)であってもよい。 (Optional component)
The solvent composition of the present invention is formed in the production process of HCFO-1233yd, 1-chloro-3,3-difluoro-1-propyne and HCFO-1233yd or 1-chloro-3,3-difluoro-1-propyne described above. In addition, components other than components difficult to separate from HCFO-1233yd or 1-chloro-3,3-difluoro-1-propyne (hereinafter simply referred to as “other components”) are within the range not impairing the effects of the present invention. You may contain. Other components include components that function as a solvent other than HCFO-1233yd that is soluble in HCFO-1233yd used for various purposes such as increasing solubility and adjusting the volatilization rate (however, 1-chloro -3,3-difluoro-1-propyne may be excluded (hereinafter referred to as “other solvents”).
本発明の洗浄方法は、上記本発明の溶剤組成物によって被洗浄物品に付着された付着物を洗浄する方法であり、本発明の溶剤組成物と被洗浄物品とを接触させることを特徴とする。 <Washing method>
The cleaning method of the present invention is a method of cleaning the deposit adhered to the article to be cleaned by the solvent composition of the present invention, and is characterized by bringing the solvent composition of the present invention into contact with the article to be cleaned. .
次に、本発明の溶剤組成物を、各種衣類の汚れの除去洗浄に用いる場合について説明する。本発明の溶剤組成物は、衣類の洗浄用溶剤、すなわち、ドライクリーニング用溶剤、として適している。 <Dry cleaning method>
Next, the case where the solvent composition of the present invention is used for removing dirt from various clothes will be described. The solvent composition of the present invention is suitable as a washing solvent for clothes, that is, a dry cleaning solvent.
本発明の溶剤組成物は、不揮発性有機化合物の希釈塗布用の溶剤(希釈塗布溶剤)に使用できる。すなわち本発明の塗膜の形成方法は、上記本発明の溶剤組成物に不揮発性有機化合物を溶解させて塗膜形成用組成物を調製し、該塗膜形成用組成物を被塗布物上に塗布した後、前記溶剤組成物を蒸発させて、前記不揮発性有機化合物からなる塗膜を形成することを特徴とする。 <Formation method of coating film>
The solvent composition of the present invention can be used as a solvent for dilute coating of non-volatile organic compounds (diluted coating solvent). That is, the method for forming a coating film of the present invention comprises preparing a coating film forming composition by dissolving a non-volatile organic compound in the solvent composition of the present invention, and applying the coating film forming composition on an object to be coated. After coating, the solvent composition is evaporated to form a coating film made of the nonvolatile organic compound.
本発明の溶剤組成物は、熱サイクルシステム用の作動媒体(熱移動媒体)として用いることができる。すなわち、本発明は、本発明の溶剤組成物を含む熱移動媒体を提供する。本発明の熱移動媒体は、物質を加熱したり冷却したりする熱サイクルシステムに適用できる。 <Heat transfer medium and heat cycle system>
The solvent composition of the present invention can be used as a working medium (heat transfer medium) for a heat cycle system. That is, this invention provides the heat transfer medium containing the solvent composition of this invention. The heat transfer medium of the present invention can be applied to a heat cycle system that heats or cools a substance.
以下、熱サイクルシステムの一例として、冷凍サイクルシステムについて説明する。 Examples of the heat cycle system include a Rankine cycle system, a heat pump cycle system, a refrigeration cycle system, a heat transport system, a secondary refrigerant cooling system, and the like.
Hereinafter, a refrigeration cycle system will be described as an example of a heat cycle system.
二次循環冷却システムとは、アンモニアや炭化水素冷媒からなる一次冷媒を冷却する一次冷却手段と、二次循環冷却システム用二次冷媒(以下、「二次冷媒」という。)を循環させて被冷却物を冷却する二次循環冷却手段と、一次冷媒と二次冷媒とを熱交換させ、二次冷媒を冷却する熱交換器と、を有するシステムである。この二次循環冷却システムにより、被冷却物を冷却できる。本発明の熱移動媒体は、二次冷媒としての使用に好適である。 Furthermore, the heat transfer medium of the present invention can also be applied to a secondary circulation cooling system.
The secondary circulation cooling system circulates a primary cooling means for cooling a primary refrigerant made of ammonia or a hydrocarbon refrigerant and a secondary refrigerant for a secondary circulation cooling system (hereinafter referred to as “secondary refrigerant”). It is a system having a secondary circulation cooling means for cooling a cooled object, and a heat exchanger for cooling the secondary refrigerant by exchanging heat between the primary refrigerant and the secondary refrigerant. An object to be cooled can be cooled by this secondary circulation cooling system. The heat transfer medium of the present invention is suitable for use as a secondary refrigerant.
撹拌機、ジムロート、冷却器、ラシヒリングを充填したガラス蒸留塔(段数測定値5段)を設置した2リットル四つ口フラスコに2,2,3,3-テトラフルオロプロパノール(TFPO)の1204g(9.12モル)およびN,N-ジメチルホルムアミド(DMF)の12g(0.17モル)を加えた。塩化チオニルの1078g(9.12モル)を滴下し、常温で12時間撹拌した。反応器を100℃に加熱し、還流タイマーにより還流時間/留出時間の比を5/1で反応蒸留を行った。留出したHCFC-244caは20質量%水酸化カリウム水溶液で中和した。回収したHCFC-244ca(純度100%)は、979g(6.50モル)であった。 (Production example: Production of HCFC-244ca)
1204 g (9,9) of 2,2,3,3-tetrafluoropropanol (TFPO) was placed in a 2 liter four-necked flask equipped with a stirrer, a Dimroth, a condenser, and a glass distillation column filled with Raschig rings. .12 mol) and 12 g (0.17 mol) of N, N-dimethylformamide (DMF) were added. 1078 g (9.12 mol) of thionyl chloride was added dropwise and stirred at room temperature for 12 hours. The reactor was heated to 100 ° C., and reactive distillation was performed with a reflux timer at a reflux time / distillation time ratio of 5/1. The distilled HCFC-244ca was neutralized with a 20% by mass aqueous potassium hydroxide solution. The recovered HCFC-244ca (purity 100%) was 979 g (6.50 mol).
2000gのHCFC-244caを原料にして、テトラ-n-ブチルアンモニウムクロリドの19.9gを入れ、反応温度を50℃に保ち、40質量%水酸化カリウム水溶液の2792gを30分かけて滴下した。その後、52時間反応を続け、有機層を回収した。回収した有機層を精製した結果、純度100質量%のHCFO-1233yd(Z)(以下、単に「HCFO-1233yd(Z)」という。)を1520g、純度100質量%のHCFO-1233yd(E)(以下、単に「HCFO-1233yd(E)」という。)を140g、1-クロロ-3,3-ジフルオロ-1-プロピンを5質量%含む混合物(残りはHCFO-1233yd(E)95質量%。以下、「混合物(X)」という。)を17g得た。この試験を繰返し実施し、必要量のHCFO-1233ydおよび1-クロロ-3,3-ジフルオロ-1-プロピンを製造した。 (Production Example: Production of HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne)
Using 2000 g of HCFC-244ca as a raw material, 19.9 g of tetra-n-butylammonium chloride was added, and the reaction temperature was kept at 50 ° C., and 2792 g of 40 mass% potassium hydroxide aqueous solution was added dropwise over 30 minutes. Thereafter, the reaction was continued for 52 hours, and the organic layer was recovered. As a result of purifying the recovered organic layer, 1520 g of HCFO-1233yd (Z) having a purity of 100% by mass (hereinafter simply referred to as “HCFO-1233yd (Z)”) and HCFO-1233yd (E) having a purity of 100% by mass (E) ( Hereinafter, a mixture containing 140 g of “HCFO-1233yd (E)”) and 5% by mass of 1-chloro-3,3-difluoro-1-propyne (the rest is 95% by mass of HCFO-1233yd (E). , "Mixture (X)") was obtained. This test was repeated to produce the required amount of HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne.
上記で得られたHCFO-1233yd(Z)、HCFO-1233yd(E)および混合物(X)を用いて、表1に示す含有割合になるように、HCFO-1233yd(Z)および/またはHCFO-1233yd(E)と、安定剤としての1-クロロ-3,3-ジフルオロ-1-プロピンを含有する溶剤組成物をそれぞれ100gずつ調製する。表1に示すHCFO-1233yd(Z)、HCFO-1233yd(E)および1-クロロ-3,3-ジフルオロ-1-プロピンの数値は、HCFO-1233ydの含有量と1-クロロ-3,3-ジフルオロ-1-プロピンの含有量の合計に対する各成分の含有量の割合(質量%)である。なお、例1~17の溶剤組成物はHCFO-1233ydと1-クロロ-3,3-ジフルオロ-1-プロピンのみからなる溶剤組成物である。 (Examples 1 to 17: Production of solvent composition (Example))
Using the HCFO-1233yd (Z), HCFO-1233yd (E), and the mixture (X) obtained above, the HCFO-1233yd (Z) and / or HCFO-1233yd are obtained so as to have the content shown in Table 1. 100 g each of a solvent composition containing (E) and 1-chloro-3,3-difluoro-1-propyne as a stabilizer is prepared. The values of HCFO-1233yd (Z), HCFO-1233yd (E) and 1-chloro-3,3-difluoro-1-propyne shown in Table 1 indicate the content of HCFO-1233yd and 1-chloro-3,3- The ratio (% by mass) of the content of each component with respect to the total content of difluoro-1-propyne. The solvent compositions of Examples 1 to 17 are solvent compositions composed only of HCFO-1233yd and 1-chloro-3,3-difluoro-1-propyne.
上記で得られたHCFO-1233yd(Z)およびHCFO-1233yd(E)を用いて、表1に示す割合でHCFO-1233yd(Z)とHCFO-1233yd(E)を含む、HCFO-1233ydのみからなる溶剤組成物を製造する。 (Examples 18 to 21: Production of solvent composition (comparative example))
Using HCFO-1233yd (Z) and HCFO-1233yd (E) obtained above, HCFO-1233yd containing only HCFO-1233yd (Z) and HCFO-1233yd (E) in the ratio shown in Table 1 A solvent composition is produced.
得られた例1~21の溶剤組成物を50℃で3日間保存する。調製直後(試験前)と保存後(試験後)の塩素イオン濃度を測定し、以下の指標で安定性を評価する。結果を表1に示す。なお、評価の指標における濃度はいずれも塩素イオン濃度である。 (Test Example 1: Stability test)
The obtained solvent compositions of Examples 1 to 21 are stored at 50 ° C. for 3 days. Chlorine ion concentration is measured immediately after preparation (before test) and after storage (after test), and the stability is evaluated using the following indices. The results are shown in Table 1. The concentrations in the evaluation index are all chloride ion concentrations.
「S(優良)」:10質量ppm未満
「A(良)」:10質量ppm以上50ppm未満
「B(やや不良)」:50質量ppm以上100ppm未満
「×(不良)」:100質量ppm以上 <Evaluation index>
“S (excellent)”: less than 10 mass ppm “A (good)”: 10 mass ppm or more and less than 50 ppm “B (somewhat poor)”: 50 mass ppm or more and less than 100 ppm “× (defect)”: 100 mass ppm or more
乾燥性については、例1~21の溶剤組成物を、常温下で鏡面仕上げしたSUS板上にパスツールピペットを用いて1滴滴下して、揮発させた際の痕跡の残り方により評価する。評価の指標は以下のとおりである。結果を表1に示す。 (Test Example 2: Dryability test)
The drying property is evaluated by dropping one drop of the solvent composition of Examples 1 to 21 on a mirror-finished SUS plate at room temperature using a Pasteur pipette and volatilizing it. The index of evaluation is as follows. The results are shown in Table 1.
「S(優良):溶剤組成物が完全に揮発して跡が残らない」
「A(良):溶剤組成物がほぼ揮発して跡が残らない」
「B(可):若干の残留物は認められるが実用上問題ない」
「×(不良):明らかな残留物が認められる」
<Evaluation index>
"S (excellent): The solvent composition is completely volatilized and no trace remains"
“A (good): The solvent composition is almost volatilized, leaving no traces”
“B (possible): Some residue is observed, but there is no practical problem”
“× (defect): obvious residue is observed”
上記で得られた例1~17(実施例)、例18~21(比較例)の溶剤組成物について、JIS K 1508-1982の加速酸化試験に準拠し、還流時間を48時間における安定性を確認する加速酸化試験を実施する。すなわち、各200mLの溶剤組成物中に、気相と液相に機械構造用炭素鋼(S20C)試験片を共存させた条件下で、水分を飽和させた酸素気泡を通しながら、電球で光を照射し、その電球の発熱で48時間還流する。 (Test Example 3: Stability evaluation test by accelerated oxidation test)
For the solvent compositions of Examples 1 to 17 (Examples) and Examples 18 to 21 (Comparative Examples) obtained above, the reflux time was 48 hours in accordance with the accelerated oxidation test of JIS K 1508-1982. Conduct an accelerated oxidation test to confirm. That is, in each 200 mL of solvent composition, light was emitted with a light bulb while passing oxygen bubbles saturated with moisture under the condition that a carbon steel (S20C) test piece for mechanical structure coexisted in a gas phase and a liquid phase. Irradiate and reflux for 48 hours with the heat generated by the bulb.
以下の、評価の指標における濃度はいずれも塩素イオン濃度である。
「S(優良)」:10質量ppm未満
「A(良)」:10質量ppm以上50ppm未満
「B(やや不良)」:50質量ppm以上100ppm未満
「×(不良)」:100質量ppm以上 <Stability evaluation index>
The concentrations in the following evaluation indices are all chloride ion concentrations.
“S (excellent)”: less than 10 mass ppm “A (good)”: 10 mass ppm or more and less than 50 ppm “B (somewhat poor)”: 50 mass ppm or more and less than 100 ppm “× (defect)”: 100 mass ppm or more
「S(優良)」;試験前後で変化なし。
「A(良)」:試験前に比べて試験後ではわずかに光沢が失われたが、実用上問題ない。
「B(やや不良)」:試験後の表面がわずかに錆びている。
「×(不良)」:試験後の表面の全面に錆びが認められる。 <Indicator for test piece appearance evaluation>
“S (excellent)”: no change before and after the test.
“A (good)”: The gloss was slightly lost after the test as compared to before the test, but there is no practical problem.
“B (slightly bad)”: The surface after the test is slightly rusted.
"X (defect)": Rust is recognized on the entire surface after the test.
上記で得られた例1~17(実施例)、例18~21(比較例)の溶剤組成物について、以下の各洗浄試験A~Dを行い、その結果を表2に示す。 (Test Example 4: Evaluation of cleaning performance)
The solvent compositions of Examples 1 to 17 (Examples) and Examples 18 to 21 (Comparative Examples) obtained above were subjected to the following cleaning tests AD, and the results are shown in Table 2.
SUS-304のテストピース(25mm×30mm×2mm)を、切削油である製品名「ダフニーマーグプラスHT-10」(出光興産株式会社製)中に浸漬した後、各例の溶剤組成物50mL中に1分間浸漬し、引き上げて切削油が除去された度合を観察する。洗浄性の評価は以下の基準に従って行う。 [Cleaning test A]
After immersing a test piece (25 mm × 30 mm × 2 mm) of SUS-304 in the product name “Daffney Marg Plus HT-10” (made by Idemitsu Kosan Co., Ltd.), which is a cutting oil, in 50 mL of the solvent composition of each example For 1 minute and pull up to observe the degree of removal of the cutting oil. Detergency is evaluated according to the following criteria.
「A(良好)」:切削油がほぼ除去される。
「B(やや不良)」:切削油が微量に残存する。
「×(不良)」:切削油がかなり残存する。 “S (excellent)”: the cutting oil is completely removed.
“A (good)”: Cutting oil is substantially removed.
“B (slightly bad)”: A small amount of cutting oil remains.
“× (defect)”: A considerable amount of cutting oil remains.
切削油として製品名「ダフニーマーグプラスAM20」(出光興産株式会社製)を使用する以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価する。 [Cleaning test B]
The test is performed in the same manner as the cleaning test A except that the product name “Daphne Marg Plus AM20” (manufactured by Idemitsu Kosan Co., Ltd.) is used as the cutting oil, and the cleaning performance is evaluated based on the same criteria.
切削油として製品名「ダフニーマーグプラスHM25」(出光興産株式会社製)を使用する以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価する。 [Cleaning test C]
The test is performed in the same manner as the cleaning test A, except that the product name “Daphne Marg Plus HM25” (manufactured by Idemitsu Kosan Co., Ltd.) is used as the cutting oil.
切削油として製品名「G-6318FK」(日本工作油株式会社製)を使用する以外は洗浄試験Aと同様に試験し、同じ基準で洗浄性を評価する。 [Cleaning test D]
The test is performed in the same manner as the cleaning test A, except that the product name “G-6318FK” (manufactured by Nippon Tool Oil Co., Ltd.) is used as the cutting oil, and the cleaning performance is evaluated according to the same criteria.
上記で得られた例1~17(実施例)、例18~21(比較例)の溶剤組成物を希釈塗布溶剤として用いて、塗膜形成用組成物(潤滑剤溶液)を調製し性能を評価する。 (Test Example 5: Evaluation of performance as a diluted coating solvent)
Using the solvent compositions of Examples 1 to 17 (Examples) and Examples 18 to 21 (Comparative Examples) obtained above as dilution coating solvents, a coating film forming composition (lubricant solution) was prepared and performance was improved. evaluate.
各例の溶剤組成物を用いた塗膜形成用組成物の溶解状態を目視で確認し、以下の基準で評価する。
「S(優良)」:直ちに均一に溶解し、透明になる。
「A(良好)」:振盪すれば均一に溶解し、透明になる。
「B(やや不良)」:若干白濁する。
「×(不良)」:白濁もしくは相分離する。 [Dissolved state]
The dissolution state of the coating film-forming composition using the solvent composition of each example is visually confirmed and evaluated according to the following criteria.
“S (excellent)”: immediately dissolves uniformly and becomes transparent.
“A (good)”: When shaken, it dissolves uniformly and becomes transparent.
“B (slightly bad)”: Slightly cloudy.
“× (defect)”: cloudiness or phase separation.
各例の溶剤組成物を用いた塗膜形成用組成物により形成される潤滑剤塗膜の状態を目視で確認して以下の基準で評価する。
「S(優良)」:均一な塗膜である。
「A(良好)」:ほぼ均一な塗膜である。
「B(やや不良)」:塗膜に部分的にムラが見られる。
「×(不良)」:塗膜にかなりムラが見られる。 [Coating state]
The state of the lubricant coating formed by the coating film forming composition using the solvent composition of each example is visually confirmed and evaluated according to the following criteria.
“S (excellent)”: a uniform coating film.
“A (good)”: A substantially uniform coating film.
“B (slightly bad)”: Unevenness is partially observed in the coating film.
“X (defect)”: The coating film is considerably uneven.
本発明の溶剤組成物を用いて、ウール生地の白色カーディガンを洗浄して洗浄性、風合いの状態を以下のように評価する。 (Test Example 5: Evaluation of washability and texture of clothing)
Using the solvent composition of the present invention, the white cardigan of the wool fabric is washed, and the detergency and texture are evaluated as follows.
Claims (11)
- 1-クロロ-2,3,3-トリフルオロ-1-プロペンと、1-クロロ-3,3-ジフルオロ-1-プロピンとを含む溶剤組成物。 A solvent composition containing 1-chloro-2,3,3-trifluoro-1-propene and 1-chloro-3,3-difluoro-1-propyne.
- 前記1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量と前記1-クロロ-3,3-ジフルオロ-1-プロピンの含有量の合計に対する1-クロロ-3,3-ジフルオロ-1-プロピンの含有量の割合が0.0001~0.1質量%である、請求項1に記載の溶剤組成物。 1-chloro-3,3-difluoro based on the sum of the content of 1-chloro-2,3,3-trifluoro-1-propene and the content of 1-chloro-3,3-difluoro-1-propyne The solvent composition according to claim 1, wherein the content ratio of -1-propyne is 0.0001 to 0.1% by mass.
- 前記溶剤組成物全量に対する1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量の割合が80質量%以上である、請求項1または2に記載の溶剤組成物。 3. The solvent composition according to claim 1, wherein a ratio of the content of 1-chloro-2,3,3-trifluoro-1-propene to the total amount of the solvent composition is 80% by mass or more.
- 前記1-クロロ-2,3,3-トリフルオロ-1-プロペンが、(Z)-1-クロロ-2,3,3-トリフルオロ-1-プロペンと(E)-1-クロロ-2,3,3-トリフルオロ-1-プロペンからなり、1-クロロ-2,3,3-トリフルオロ-1-プロペン全量に対する(Z)-1-クロロ-2,3,3-トリフルオロ-1-プロペンの含有量の割合が80~100質量%である、請求項1~3のいずれか一項に記載の溶剤組成物。 The 1-chloro-2,3,3-trifluoro-1-propene is represented by (Z) -1-chloro-2,3,3-trifluoro-1-propene and (E) -1-chloro-2, (Z) -1-chloro-2,3,3-trifluoro-1-based on the total amount of 1-chloro-2,3,3-trifluoro-1-propene consisting of 3,3-trifluoro-1-propene The solvent composition according to any one of claims 1 to 3, wherein a proportion of the propene content is 80 to 100% by mass.
- 請求項1~4のいずれか一項に記載の溶剤組成物と被洗浄物品とを接触させることを特徴とする洗浄方法。 A cleaning method comprising contacting the object to be cleaned with the solvent composition according to any one of claims 1 to 4.
- 前記被洗浄物品に付着した加工油を洗浄する、請求項5に記載の洗浄方法。 The cleaning method according to claim 5, wherein the processing oil adhering to the article to be cleaned is cleaned.
- 前記加工油が、切削油、焼き入れ油、圧延油、潤滑油、機械油、プレス加工油、打ち抜き油、引き抜き油、組立油および線引き油からなる群より選ばれる1種以上である、請求項6に記載の洗浄方法。 The processing oil is at least one selected from the group consisting of cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, pressing oil, punching oil, drawing oil, assembly oil, and drawing oil. 6. The cleaning method according to 6.
- 前記被洗浄物品が衣類である、請求項5~7のいずれか一項に記載の洗浄方法。 The cleaning method according to any one of claims 5 to 7, wherein the article to be cleaned is clothing.
- 請求項1~4のいずれか一項に記載の溶剤組成物に不揮発性有機化合物を溶解させて塗膜形成用組成物を調製し、該塗膜形成用組成物を被塗布物上に塗布した後、前記溶剤組成物を蒸発させて、前記不揮発性有機化合物からなる塗膜を形成することを特徴とする、塗膜の形成方法。 A non-volatile organic compound is dissolved in the solvent composition according to any one of claims 1 to 4 to prepare a coating film forming composition, and the coating film forming composition is applied onto an object to be coated. Then, the solvent composition is evaporated to form a coating film made of the non-volatile organic compound.
- 請求項1~4のいずれか一項に記載の溶剤組成物を含む熱移動媒体。 A heat transfer medium comprising the solvent composition according to any one of claims 1 to 4.
- 請求項10に記載の熱移動媒体を用いた熱サイクルシステム。 A heat cycle system using the heat transfer medium according to claim 10.
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US16/515,770 US10807926B2 (en) | 2015-07-27 | 2019-07-18 | Solvent composition, cleaning method, method of forming a coating film, heat transfer fluid, and heat cycle system |
US17/020,652 US11440862B2 (en) | 2015-07-27 | 2020-09-14 | Solvent composition, cleaning method, method of forming a coating film, heat transfer fluid, and heat cycle system |
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